Just when you thought Steve Bannon had finally achieved the political obscurity his rumpled suits so richly deserve, 2025 came along and proved that the man has the gravitational pull of a black hole made of bad ideas and unwashed collar shirts.
December brought us a gift no one asked for: a fresh batch of photos from the late, great convicted sex offender Jeffrey Epstein’s estate . And there, like a stain that just won’t come out, was Stephen K. Bannon. In one particularly artistic shot, Bannon is pictured with Epstein taking a photograph in a mirror . It’s a fitting metaphor—two men, reflecting each other’s ambition and poor judgment, trapped in a frame they can’t escape.
The “Amazing Assistant” and His Boss
Of course, Bannon wants you to know he wasn’t friends with Epstein. He was just using him for logistics. Previously released emails from the Epstein trove showed Bannon frantically messaging the pedophile financier in 2018 because protesters delayed his speech at the Oxford Union and he was worried about missing his flight.
Epstein, ever the helpful concierge, replied: “There is a gulf air that leaves at 950 with a stop in Bahrain.”
Bannon’s response? “U r an amazing assistant” .
Yes, the man who styled himself as the heir to Andrew Breitbart, the man who was going to burn down the administrative state, was so flustered by a few college protesters that he had to ask a convicted sex offender for travel tips. To be fair, it’s hard to find good help when your Rolodex is 90% political operatives and 10% international criminals.
Bannon, the Westerhout Scandal, and a Whole Lot of “Creepy”
But Bannon’s 2025 wasn’t just about photobombing Epstein’s vacation album. He also managed to insert himself into one of the year’s most awkward political stories involving former aide Madeleine Westerhout.
Author Michael Wolff (the man who makes Bannon look well-groomed by comparison) shared a draft of a book with Epstein via email back in 2019 . In it, Wolff alleged that President Trump stayed in Washington during the 2018 Christmas shutdown, where a 28-year-old Westerhout would find him in the residence—according to her telling friends—”in his underwear” .
But who allegedly noticed Trump’s “particular interest” in the young aide? Who recalled that Trump “kept repeating, ‘She’s got a way about her'”?
That’s right. Steve Bannon .
Wolff described this as Trump’s “signature, and creepy, stamp of approval for young women” . And Bannon was there to witness it, catalog it, and presumably, store it away for future use. It’s a beautiful glimpse into the locker room atmosphere of the early Trump White House, with Bannon lurking in the background, taking mental notes while probably wearing three shirts and zero deodorant.
(Westerhout, to her credit, dismissed these claims as “absurd” and “unhinged from reality,” which is a polite way of saying “Michael Wolff wrote it, so take it with a grain of salt the size of Bannon’s ego” .)
The Origin Story of “Sloppy Steve”
All of this brings us back to the nickname. The one that hurts the most because it’s so visually accurate.
When Trump finally booted Bannon from the White House in August 2017, it wasn’t just a firing; it was a branding event. After Bannon was quoted in Wolff’s book “Fire and Fury” calling a Trump Tower meeting with Russians “treasonous,” the President unleashed his ultimate weapon: the nickname generator .
Thus, “Sloppy Steve” was born .
It was perfect. It was a dig at his unshaven appearance, his tendency to wear three collared shirts like he was preparing for a sartorial apocalypse, and his general lack of polish . Trump, the germaphobe who likes his steaks well-done and his aides well-pressed, was horrified by the human laundry pile he had accidentally hired.
The nickname stuck because it was true. You can’t spin “Sloppy.” You can’t rebrand it. You can only wear it—usually wrinkled and untucked.
The Sloppy Legacy
So here we are. Steve Bannon: a man who appears in Epstein photos despite having “no wrongdoing” alleged . A man who was in the room for some of the weirdest, creepiest moments of the Trump presidency. A man who was so disposable that his boss reduced his entire identity to a critique of his hygiene and wardrobe .
He’s since tried to stay relevant with his “War Room” podcast and by threatening to drive Elon Musk out of the White House, but let’s be honest: his legacy is sealed. He’s the guy who called a pedophile an “amazing assistant.” He’s the guy who thought Trump’s “she’s got a way about her” comments were worth remembering. And he’s the guy who will forever be known as “Sloppy Steve”—a nickname that manages to insult his politics, his person, and his packing skills all at once.
Here’s to you, Steve. May your mirrors always reflect the company you keep, and may your laundry bill finally catch up with you.